Water → HCID 178448728, compound

HRID 1906370Notes

Reaction equation

HRID 1906370 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:12]([N:16]=[C:17]=[S:18])[CH2:13][CH2:14][CH3:15].O>CN(C)C=O>[CH2:12]([N:16]1[C:1](=[O:10])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=[C:17]1[SH:18])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 8635Methyl AnthranilateHCID 11613Butyl Isothiocyanate

Product 1

HCID 178448728HCID 178448728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 7.6 g (0.05 mole) methyl anthranilate and 5.8 g (0.05 mole) n-butyl isothiocyanate in 45 ml dimethylformamide was heated at reflux for 11/2 hours, stirred overnight, then heated for 6 hours and then stirred at ambient temperature over the weekend. The reaction mixture was poured into 200 ml water (at 20° C.) to give a precipitate. The mixture was chilled and then filtered. The precipitate was washed three times with water; the filtrate was set aside. A small amount of ethanol was drained through the filter cake once. The solid was washed twice with hexane and air-dried overnight to give the above-identified product, as a solid, melting point 167°-172° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11/2 hours
  3. temperatureheated for 6 hours
  4. stirringstirred at ambient temperature over the weekend
  5. customto give a precipitate
  6. temperatureThe mixture was chilled
  7. filtrationfiltered
  8. washThe precipitate was washed three times with water
  9. washThe solid was washed twice with hexane
  10. customair-dried overnight
  11. customto give the above-identified product

Sources & evidence

ORD record
ord-e5f9fe1c13ca42d68a1e878afc151af0
Source dataset
uspto-grants-1987_03
Patent number
US04652558

Reaction notes

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